Augustine was aware of objections to the idea of educational progress, and nowhere is this more acute than in his treatment of academic skepticism. While much attention has been paid to Augustine’s theory of knowledge within the Contra Academicos, too often overlooked is the specifically moral significance that he attaches to the skeptic’s critique of knowledge. I argue that Augustine’s chief criticism in this dialogue is not directed against an erroneous epistemology, although he does provide a refutation of that. Rather, itis against the disastrous educational and moral implications that follow from the skeptic’s views. Along the way I show how this interpretation helps to explain some of the novel structural features of the dialogue and allows us more securely to situate its argument against Augustine’s other key early reflections on the limits of knowledge